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Twice a year, the medieval streets of Siena, Italy turn into the battleground for the Palio.

ByLee Marshall on December 14, 2015

In a distant land, a talented young horseman arrives at the gates of an ancient walled city. He’s a foreigner, drawn here by an equestrian tournament that, for the winner, holds out the promise of rich earnings and eternal glory. But this is not a free and fair contest; it’s a nest of vipers, a den of intrigue, presided over by a sly old fox of a fantino (jockey) whose web of influence spreads and chokes like bindweed. The older man offers to coach him, and the beginner accepts what he knows to be a pact with the devil. Will the wily elder statesman manage to keep his new charge under his thumb? Or will the young pretender be able to break away, turn the tables on his canny master and win the prize?

It sounds like a fantasy action movie with shades of Gladiator and Game of Thrones. Instead, it’s the storyline of one of the year’s most talked-about documentaries: Palio, by Anglo-Italian filmmaker Cosima Spender.

The two jockeys are regular contestants in Siena’s celebrated twice-yearly horse race, the Palio. The young pretender is 30-year-old half-Sardinian, half-German rider Giovanni Atzeni (nicknamed Tittìa), the wily old veteran, 47-year-old Sienese Gigi Bruschelli (dubbed Trecciolino), whose record of 13 victories makes him one of the most successful Palio riders of all time. Spender tracked the two in the buildup to the 2013 races, interlacing their stories with interviews with retired jockeys, Palio racehorse owners like Getty Images cofounder and deputy chairman Mark Getty, and some ravishing training and race footage.

The film’s third main character is Siena itself, a city accurately described by 19th-century French writer Hippolyte Taine as “a medieval Pompeii”—though it’s a vibrant, living example of the genre. Radiating from conch-shaped central Piazza del Campo, where the Palio takes place, cultured Siena is a hilltop city of winding lanes that feel like urban canyons.

It’s a place that (as travelers soon discover) can take some getting to, given its out-of-the-way location south of the Chianti wine region, a fair distance west of Italy’s main Florence-to-Rome freeway and high-speed-rail link. Only slow trains pull in here, quite literally, and one suspects the Sienese like it that way. But such isolation has its upside: A restaurant like Osteria Le Logge, a historic artists’ haunt just off the Campo and the essential place for a pre- or post-Palio meal, would risk being sunk by its own cult status in Florence. Here, it stays grittily authentic—while championing carefully sourced market ingredients and a wine list that would be the envy of many luxury-hotel cellars.

Like Pompeii, Siena suffered an eruption of sorts in 1555, the year in which it finally capitulated to Spain, who then handed over the proud city-state to its great rival, Florence. Thereafter, the Sienese—who had practically invented the modern banking system in the 13th century—became more inward looking, falling back on the Palio, in particular, to mark themselves off from the rest of Medici Tuscany, and turning the race into a symbolic touchstone of difference by making it so complex no outsider could possibly understand it.

For travelers, the Palio is a colorful garnish to a summer holiday in Tuscany. Around a week before each of the two summer races, a special mix of fine sand and volcanic limestone is spread around the perimeter of the Campo and compacted to form the racetrack. “C’è laterra in piazza” (the earth’s been laid in the square), the Sienese say to one another excitedly. It’s perhaps not too fanciful to see, in this acknowledgement of the way their much-loved piazza can be transformed, the locals’ recognition of the space as a kind of civic theater, dominated on one side by the city’s medieval seat of government, the Palazzo Pubblico, and ringed on the other by a crescent of café and restaurant terraces that provide perfect views of a stage where entertainment is provided, most of the year, by children chasing pigeons. At Palio time these chairs and tables are replaced by grandstand seats that are almost impossible to book unless you’re at least third-generation Sienese, while the windows and balconies of the houses surrounding the square become high-class theater boxes, with prices to match.

An estimated 60,000 spectators pack into the Campo on race day. Those who don’t have the right contacts or can’t afford the asking price for the bleachers or window seats are penned into the central enclosure—known locally as il palco dei cani, “the dogs’ stand.” They need to be in position well before the start of the historical parade—a colorful but drawn-out affair that takes around three hours. And it’s not as if the race begins immediately afterward. Once the horses enter the Campo, to appreciative cheers, a protracted phase at la mossa (the starting line) gets under way.

This process can be baffling to outsiders, as the ten horses, each ridden by a jockey wearing the colors of a different contrada, or city district, repeatedly fail to line up at the starting rope. As Spender’s documentary explains—and it’s this mediation between what we see and what’s really happening that is the film’s engaging raison d’être—the delays are purely tactical. As for the explosive three-lap race, this is often even more of a mystery to those not born within Siena’s walls: a thunder of hooves, a blur of team colors, the frantic thrash of whips (used not only on the horses but on other jockeys), and in little more than a minute it’s all over, with delirious contradaioli (contrada residents) from the winning district running to mob their horse and jockey.

I wanted to go beyond the postcard,” says Spender, who grew up in the countryside outside Siena with her artist parents. Sculptor father Matthew was the inspiration for the Jeremy Irons character in Bernardo Bertolucci’s 1996 film Stealing Beauty; painter mother Maro is the daughter of abstract-expressionist Arshile Gorky. It’s Matthew—a writer as well as a sculptor—who puts his finger on what lies beyond the postcard when he confides, over lunch at Casa Spender, that “the Palio is like the equestrian version of Dante’s Inferno.”

It’s not just the names of the contrade— based on chivalric emblems such as the chiocciola (snail) or istrice (porcupine)–rooting the Palio in the Middle Ages. Born out of the medieval guild system, the Sienese contrade are in effect micro local mutual-aid societies: contradaioli submit willingly to a self-taxing system, not only in order to raise the money it takes to win a Palio, but also to help out other contradaioli: Spender cites the case of a girl from the Aquila (eagle) district whose cancer treatment at a clinic in Rome was paid for out of voluntary contrada contributions. “Siena must be the only city in Italy,” she says, “that could happily function without a government.”

Palio, the film, elegantly sketches in the seemingly bottomless complexities of a race that Spender calls “Italy in a nutshell”; for example, in the way that “the contrada is more important than the individual,” or in “the wheeler-dealing, the bribery...which is not even seen as bribery, it’s just seen as human relationships.”

Traditionally, there is no betting on the race; neither is there any prize money, with the winning team receiving only a painted banner—the palio. And yet rivers of money flow in various directions before, during, and after. The before and after are the easiest to grasp. Prerace, the horses are assigned by lot to the ten competing contrade four days before the Palio, at which point a frantic “jockey market” opens up, with each district aiming to engage, at a price, the best fantino. After, high on adrenaline, the victorious contrada, Spender explains, “pays everyone else off for favors received, or just to show off their bravado.”

Spender befriended many contradaioli during the filming, and was even “baptized” into the Aquila contrada. But in the end, she says, her loyalties remain firmly with the fantini. “I liked that the jockeys were these ambivalent characters who are both loved and hated by the citizens. I thought their despised but also revered position in the eye of the storm was interesting.” Could her own experience of being raised in Tuscany by foreign parents have led her to siding with these insider-outsiders? “Definitely. The reason I picked Giovanni, for example, was because he was half German and half Sardinian, and I thought we have something in common...this idea of being half-and-half.”

Sent to school in Siena at the age of 11, the director also has personal experience of the divide between the Tuscan countryside, where the horses are stabled and the jockeys train, and a “very difficult city...where everything happens behind closed doors. Imagine training in these stunning landscapes all year round, being in this Eden...then you get to Siena and it’s like the Minotaur’s labyrinth.”

Getting the Best View of the Palio

The annual Palio races take place on July 2 and August 16, but it’s worth arriving in Siena at least two days before to catch the build-up in the piazza; it’s also worth keeping one’s departure flexible—rain can sometimes cause a one-day postponement, as it did this past August.

It is possible to view the race for free from the center of the Piazza del Campo, but to do so, one should turn up before 3 p.m. and prepare for a wait of at least three hours—often in the blazing sun— in an area with no toilet facilities. The civilized option is to reserve a seat in one of the grandstands, or at one of the balconies or windows of the houses that look onto the piazza. Grandstand seats start at around $280 per person, window or balcony seats at around $450, depending on sight lines and elbow room. However, don’t assume these are just a click away; as Amy Lehman, who is married to a Sienese, says, “getting Palio seats is a bit of a Palio in and of itself.”

The best advice is to contact a Siena insider like Emily Fitzroy (emily@bellinitravel.com) of Bellini Travel, whose Palio experience (complete with butler and race commentary from a local maven) offers what are probably the best views, from the windows of Contessa Cesarina d’Elci’s palazzo, overlooking the start and finish line. The package starts at $5,500 per person. Other good contacts are Palio-expert Jacopo della Torre (jacopodellatorre.com) and Nabil El Sayed (concierge.continental@niquesa.com), of the Grand Hotel Continental, who can sometimes find tickets for hotel guests as late as a month before the race. But for the best spots, aim to book at least a year in advance.